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Are Buyers or Vendors the Bigger Source of Software Purchase Regret?

Written by Tom Ryan

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A global survey of over 3,500 businesses from Capterra found that 48% regret at least one software purchase made in the last 18 months.

Of the regretful software buyers, 63% described the financial impact of the investment as “significant to monumental.” The top impacts of purchase regret for businesses include higher costs cited by 49%, security vulnerability and reduced productivity at 42% each, adoption challenges cited by 39%, and competitive disadvantage at 34%.

The survey still found that 73% of organizations plan to increase their software spending in 2025, with a significant focus on IT systems and AI.

Key factors contributing to (or mitigating) purchase regret include:

  • An oversaturated AI market: With the rapid growth of AI-supported software options, the number of buyers struggling to evaluate the value and risks of GenAI tools has jumped 70% year-over-year.
  • Unclear goals: Buyers who regret their purchases cite the need for better goal-setting (36%) and stronger stakeholder alignment (32%) before making decisions.
  • Decision paralysis: Most successful buyers (57%) take three months or less to evaluate their software options, while most regretful buyers (54%) take five months or longer.
  • Prior software experience and user reviews: Successful buyers are 50% more likely to include prior software experience in their initial evaluations and place significant weight on vendor reputation. Regretful buyers, however, tend to focus more on ads and social media.
  • Product trials: Free product trial periods (going beyond demos) offer companies an optimal opportunity to test functionality and ease of use before purchase. Successful buyers are 25% more likely to factor product trials in their final purchase decision versus regretful buyers.

Gartner’s “Why Software Buyers Experience Regret” report last year similarly found that three in five buyers regretted a software purchase within the previous 18 months. However, Gartner’s study found software vendors equally at fault for not managing expectations.

Capterra’s study found that 88% of regretful software buyers say they are likely to purchase software based solely on information they get directly from vendors.

Warning signs in the sales pitch process that may indicate potential regret from buyers, according to Gartner, include overconfidence in the product, inexperience in the business, a failure to use product comparison sites, or businesses that are clearly in an accelerated growth stage.

Thibaut de Lataillade, global VP of products at Gartner Digital Markets, told TechRepublic, “The primary concern here is the unexpected cost or total cost of ownership, which customers often do not fully understand due to lack of transparency in costing of some of these software products. Customers often do not know about the additional costs that may come from product implementations, configurations, integrations and training needed to use the software.”

The top vendor-related factors driving regret include problematic handoff between sales and implementation (43%) and mismanaged expectations (42%). Lataillade added, “Both factors can quickly sour the post-purchase experience, leading to dissatisfaction. The implications of such dissatisfaction are not confined to a mere transaction but extend to the heart of strategic business decisions.”

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